Synthesis and biological evaluation of nojirimycin- and pyrrolidine-based trehalase inhibitors

Year: 2012

Authors: Bini D., Cardona F., Forcella M., Parmeggiani C., Parenti P., Nicotra F., Cipolla L.

Autors Affiliation: Department of Biotechnology and Biosciences, University of Milano-Bicocca, Piazza della Scienza 2, 20126 Milano, Italy;
Department of Chemistry “Ugo Schiff”, University of Florence, Polo Scientifico e Tecnologico, Via della Lastruccia 3–13, 50019 Sesto Fiorentino, Florence, Italy;
CNR-INO U. O. S. Sesto Fiorentino c/o LENS, Via Nello Carrara 1, 50019 Sesto Fiorentino, Florence, Italy;
Department of Environmental Sciences, University of Milano-Bicocca, Piazza della Scienza 1, 20126 Milano, Italy

Abstract: A small set of nojirimycin- and pyrrolidine-based iminosugar derivatives has been synthesized and evaluated as potential inhibitors of porcine and insect trehalases. Compounds 12, 13 and 20 proved to be active against both insect and porcine trehalases with selectivity towards the insect glycosidase, while compounds 10, 14 and 16 behaved as inhibitors only of insect trehalase. Despite the fact that the activity was found in the micromolar range, these findings may help in elucidating the structural features of this class of enzymes of different origin, which are still scarcely characterised.


Volume: 8      Pages from: 514  to: 521

More Information: We gratefully acknowledge University of Milano-Bicocca FAR 2009, MIUR (PRIN2008/24M2HX) and Ente CRF for financial support.
KeyWords: glycosidases inhibitors; iminosugars; nojirimycins; pyrrolidines; trehalases
DOI: 10.3762/bjoc.8.58

Citations: 22
data from “WEB OF SCIENCE” (of Thomson Reuters) are update at: 2022-11-27
References taken from IsiWeb of Knowledge: (subscribers only)
Connecting to view paper tab on IsiWeb: Click here
Connecting to view citations from IsiWeb: Click here